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Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

The enantioselective tandem Friedel–Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)(2) complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to hig...

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Detalles Bibliográficos
Autores principales: Peng, Jiahuan, Du, Da-Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3701415/
https://www.ncbi.nlm.nih.gov/pubmed/23843916
http://dx.doi.org/10.3762/bjoc.9.137
Descripción
Sumario:The enantioselective tandem Friedel–Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)(2) complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).